What: The 39th annual Toronto International Film Festival

a.k.a.: TIFF

When: September 4 - 14

Why: Traditionally, the Toronto Film Festival was the kick-off to Oscar Season, with the big awardsy movies setting themselves up for the final few months of the year. In recent years, and to no small amount of consternation from the TIFF folks, other film festivals have been eating their lunch. Last year's two top Oscar contenders — 12 Years a Slave and Gravity — made their world premieres at Telluride and Venice, respectively. This year, again, a lot of what might have otherwise been feathers in Toronto's cap found their way to the Rockies, most prominently Reese Witherspoon in Wild and Benedict Cumberbatch in The Imitation Game. Both those films will still play TIFF (as 12 Years a Slave did last year), but you get the sense that up in Toronto they're kicking at the dirt, mumbling about how things used to be different. 

In 2014, it seems that everybody's just going to have to get used to sharing festival films, and Toronto (which will screen nearly 400 films in total) is big enough to absorb the blow of some premiere snatching. 

TIFF Movies That Have Played Previous Festivals
Cannes Telluride Venice
The Clouds of Sils Maria 99 Homes 99 Homes
Foxcatcher Foxcatcher Good Kill
Leviathan The Imitation Game Far From Men
Maps to the Stars The Look of Silence Hungry Hearts
Mr. Turner Madame Bovary The Look of Silence
Mommy Mr. Turner Manglehorn
The Search Mommy Passolini
Still the Water Rosewater A Pigeon Sat on a Branch ...
Timbuktu Two Days, One Night Red Amnesia
Winter Sleep Wild

Three Hearts

Who Wins? Unlike something like Cannes, TIFF is not a competitive film festival strictly speaking, but they do have their People's Choice Award, which is voted on by the audiences.

Does It Matter Who Wins? Sort of? While the Opening Night films don't usually make much of a splash in awards season (sorry, The Judge), the People's Choice winners have a much better track record. In the six years since Slumdog Millionaire took the award in 2008, People's Choice Winners have been Best Picture nominees at the Oscars five time and have won that category thrice (SlumdogThe King's Speech12 Years a Slave). In their most relevant years, TIFF's audience award serves as a springboard to launch an Oscar campaign, as was the case with Silver Linings Playbook two years ago. 

Which Movies Are Looking to Break Out of TIFF This Year? I mean, all of them? The two biggest potential Oscar players at TIFF, Wild and Foxcatcher, have already bowed elsewhere, as has the Best Actor campaign for Benedict Cumberbatch in The Imitation GameBut, yes, there are still quite a few TIFF premieres that have serious awardsy ambitions. 

  • Black and White: Director Mike Binder and stars Kevin Costner and Octavia Spencer come together in this story of a custody battle for a granddaughter after a tragedy. Costner's been taking baby steps at a major comeback for almost a decade now, but the best he's been in that span was in Binder's The Upside of Anger, so there's some cause for optimism here.
  • The Last Five Years: While seemingly not much of a threat to this year's awards campaign, this musical adaptation starring Anna Kendrick and Jeremy Jordan could get a nice buzzy jump on a 2015 release, particularly if it finds a distribution deal.
  • Men, Women and ChildrenJason Reitman's latest boasts a spectacular cast — Adam Sandler, Emma Thompson, Jennifer Garner, Judy Greer, Rosemarie DeWitt, Ansel Elgort, J.K. Simmons — but after last year's Labor Day fiasco, it's hard to imagine Reitman's name is the most trusted one in the business. That trailer really does make the movie look like a slog. (But those actors!)
  • The Theory of EverythingThere have been rumblings of an Oscar race between skinny Brits playing geniuses in biopics, with Benedict Cumberbatch (The Imitation Game) going up against Eddie Redmayne's performance here as Stephen Hawking. Raves for Redmayne, or Felicity Jones as Hawking's wife, could put them in the thick of the acting categories.
  • St. Vincent: Bill Murray and Melissa McCarthy are the draws for this downbeat comedy. Everybody assumed that Lost in Translation had opened the doors for an inevitable Murray Oscar, but that never panned out. He's playing a loveable old grump here, which can be catnip for Oscar voters if packaged the right way.
  • While We're YoungNoah Baumbach is coming off the best film of his career in Frances Ha. Now he's back with Ben Stiller (a Greenberg reunion) and Naomi Watts in what looks like a less manic version of This Is Forty (hopefully a less crappy version too). Amanda Seyfried, Adam Driver, and a career-resurgent Charles Grodin co-star. 
  • NightcrawlerJake Gyllenhaal plays an off-kilter (and maybe unhinged?) crime reporter in what could end up being a real acting showcase, for good or ill.
  • Time Out of Mind: Richard Gere playing a homeless man in New York sounds like the makings of the worst kind of cynical awards bait. But director Oren Moverman, who delivered muscular, probing films with The Messenger and Rampart, is a reason to hope for the best.
  •   A Little ChaosThe closing-night film of the festival is Alan Rickman's directorial effort, starring Kate Winslet as a landscape architect in the court of Louis XIV. No one is talking about this one, which either means expectations are low or it's going to be a huge surprise.
  • The Reach: Here's the description from the TIFF guide: "A high-rolling corporate shark (Michael Douglas) and his impoverished young guide (Jeremy Irvine, War Horse) play the most dangerous game during a hunting trip in the Mojave desert." A career nod for Michael Douglas is never out of the question, but at the very least this sounds like delicious junk, right? The most dangerous game!
  • The Riot Club: Director Lone Scherfig followed up her breakthrough Best Picture nominee An Education with the rather terrible romantic dramady One Day. So The Riot Club is shaping up as something of a rubber match. A "scathing dissection" (per its TIFF summary) of the British class system via elite and debaucherous Oxford students and starring a bunch of up-and-comers like Natalie Dormer, Sam Claflin, Holliday Grainger, Jessica Brown Findlay, Douglas Booth, and Max Irons, this could easily make a star out of someone before the festival is out. 
  • Miss Julie: Screen legend Liv Ullman directs this August Strindberg adaptation starring Jessica Chastain and Colin Farrell. Chastain is always a threat to deliver a breakout performance, so a lot of eyes will be on this one.